反応 #2175425

反応方程式

ammonia

Lithium aluminum hydride

trans-4-(4-Hexyloxy-2,3-difluorophenyl)-cyclohexanecarboaldehyde

ethyl acetate

→

trans-4-(4-hexyloxy-2,3-difluorophenyl)-hydroxymethylcyclohexane

収率 29.6%

溶媒

THF

反応条件

後処理

1. 1
   温度cooling
2. 2
   その他deposits were removed by filtration through Celite
3. 3
   抽出The filtrate was extracted with ethyl acetate
4. 4
   洗浄The combined organic phase was washed successively with water and brine
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   その他the residue was purified by recrystallization from heptane

実験手順

Lithium aluminum hydride (1.1 g) was suspended in THF (200 ml). trans-4-(4-Hexyloxy-2,3-difluorophenyl)-cyclohexanecarboaldehyde (s-15) (15.8 g) was added dropwise to the suspension in the temperature range of −20° C. to −10° C., and the stirring was continued in this temperature range for 2 hours. After the completion of the reaction had been confirmed by means of GC analysis, ethyl acetate and then a saturated aqueous solution of ammonia were added to the reaction mixture under ice-cooling and deposits were removed by filtration through Celite. The filtrate was extracted with ethyl acetate. The combined organic phase was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by recrystallization from heptane to give trans-4-(4-hexyloxy-2,3-difluorophenyl)-hydroxymethylcyclohexane (s-16) (4.7 g). The yield based on the compound (s-15) was 29.6%.

出典